Cuba is trapped between a rock, a hard place, and Donald Trump. Given their options, making a deal with President Trump is their best bet.
As we know, Cuba has been a communist thorn in the side of the United States for decades. When Fidel Castro died in 2016, there were hopes that finally, something would begin to change. But nothing really did, even though Barack Obama had completely kissed up to Cuba during his administration. But now, with Trump pushing his “Don-roe Doctrine” for the Western Hemisphere, with Secretary of State Marco Rubio right there, it does feel like change is in the air.
"I want to thank the countries that are here today. These countries—first, the President has made this region a priority in his administration. There are many presidents who have said they are going to do it, but he has done it, and we are very grateful to the 12 countries that…
— Tired of being politically correct (@USBornNRaised) March 7, 2026
So let’s look at the rock and the hard place, and then see what President Trump and his administration might be offering.
Cuba was dependent on their allies Venezuela, Russia, and China to keep them afloat economically and protected from the United States. Well, things have changed. Nicolas Maduro is now in American custody, and President Trump has the Venezuelan oil that Cuba depended on under his control. Russia, who has been an ally of Cuba for decades, still talks a big game when it comes to protecting them. But since Russia has now been bogged down in years of war with Ukraine, and has only offered intelligence to Iran while their “partner” (not ally, apparently) is being bombed, I don’t think Russia is going to be running to the rescue. And China, though they love the proximity of Cuba to the United States for their own nefarious purposes, just offered thoughts and prayers to their Iranian friends, who supplied them with oil. China has said that they will “help,” but that might mean saying “it’s been great, best of luck” and stop taking their calls when faced with actually confronting the United States’ blockade. Trump has upended the scales with the arrest of Maduro and Operation Epic Fury in Iran, and now the communist regime in Cuba is suddenly finding themselves very alone and very geographically close to the United States.
Thanks to Cuba’s dependence on imported resources, their economy is in shambles. Their electrical grid has been struggling for years, and now the lack of oil has created more power outages. What happens when a communist government fails to deliver, while other countries are seeing their dictators fall? Usually, revolution.
Freedom and hope are contagious.
It’s a chain reaction. The people of Syria saw Sinwar defeated. The people of Venezuela saw Assad fall. The people of Iran saw Maduro arrested. The people of Lebanon and Cuba have seen Khamenei fall.
The world is changing. https://t.co/jvyHnyhBDG
— AG (@AGHamilton29) March 9, 2026
Are the Cuban people inching ever closer to throwing off the Castros and the regime that they have lived under since 1959? One can guess that the Cuban communist regime is desperately hoping to find a way to avoid being overthrown or having Raul Castro snatched away.
So, stuck between a rock and a hard place, Cuba may be offered a third option.
Obviously, Secretary of State Marco Rubio has a vested interest in seeing the Cuban regime finally fall into the dustbin of history. Axios reports that Rubio has been talking with Raul Castro’s grandson to see what kind of progress can be made off the clock.
Secretary of State Marco Rubio has been holding secret talks with the grandson and caretaker of Cuba’s aging de facto dictator, Raul Castro, as the U.S. puts unprecedented pressure on Havana’s regime, three sources tell Axios.
The talks between Rubio and Raul Guillermo Rodriguez Castro are bypassing official Cuban government channels. They show that the Trump administration sees the 94-year-old revolutionary as the communist island’s true decision-maker.
“I wouldn’t call these ‘negotiations’ as much as ‘discussions’ about the future,” a senior Trump administration official said.
Rubio and his team see the 41-year-old grandson and his circle as representing younger, business-minded Cubans for whom revolutionary communism has failed — and who see value in rapprochement with the U.S.
“Our position — the U.S. government’s position — is the regime has to go,” the senior official said. “But what exactly that looks like is up to [President Trump] and he has yet to decide. Rubio is still in talks with the grandson.”
Called “Raulito,” the younger Castro is known in political circles by his nickname “El Cangrejo” (“The Crab”) because he has a deformed finger.
Obviously, President Trump is fully aware of Rubio’s discussions, and is anticipating change in Cuba.
“As we achieve a historic transformation in Venezuela, we’re also looking forward to the great change that will soon be coming to Cuba,” Trump said on March 7. “Cuba’s at the end of the line, they’re very much at the end of the line. They have no money. They have no oil. They have a bad philosophy; they have a bad regime that’s been bad for a long time.”
Trump has called on Cuban leaders in the weeks since to “make a deal” and said Secretary of State Marco Rubio, who’s Cuban American, is engaging at “a very high level” with Havana. He reiterated those talks at the summit, at one point suggesting that Rubio take time off to “finish up a deal on Cuba.”
“They want to negotiate, and they are negotiating with Marco and myself and some others, and I would think a deal would be made very easily with Cuba, but for 50 years, I’ve been hearing…about Cuba,” Trump said at the summit. “Cuba’s in its last moments of life as it was. It’ll have a great new life, but it’s in its last moments of life the way it is.”
In a moment that earned applause from the crowd of world leaders, Trump added that he would “take care” of Cuba for the other Latin American countries.
“Many of you have come today and they say, ‘I hope you can take care of Cuba’ because you’ve had problems with Cuba, right, you mentioned. I was surprised, but four of you said, actually, ‘Could you do us a favor? Take care of Cuba.’ I’ll take care of it, okay?” he said.
To that end, a USA Today report is claiming that Trump is prepared to make an economic deal with Cuba in order to speed up regime change.
The details of the prospective deal and exact timing are not known. But an agreement could include a relaxation on Americans’ ability to travel to Havana. Trump would not need Congress’ approval to loosen those types of restrictions.
Discussions have included an off-ramp for President Miguel Díaz-Canel, the Castro family remaining on the island and deals on ports, energy and tourism. The U.S. government has floated dropping some sanctions.
Trump has been warning of the Cuban government’s downfall since his administration struck Venezuela and snatched Maduro in a secret raid on his compound. Trump said in January that the United States didn’t need to take military action in Cuba because the country would collapse economically if it were unable to rely on Venezuela.
Trump has leverage that Obama didn’t have, the people familiar with ongoing discussions said.
The administration has ratcheted up pressure on Cuba’s government in recent days with thinly veiled warnings that it could indict Cuban government officials.
Now, will Cuban leaders acknowledge that Trump is offering them a way out? Well, Iran was offered a way out, and they refused to take it. This is not to say that Trump is going to turn around and bomb Cuba, but dictators don’t like giving up their power. They either have to be bribed, coerced, or convinced that they have no other alternative. The Trump administration is definitely cutting off or blocking any avenues of assistance that Cuba would have appealed to in the past. There are some people in the streets, and there is always the possibility that others will join them. When a regime that controls everyday life can’t provide the basics, the people usually have something to say about it. Will Rubio’s backchannel chats bear fruit? Will the economic deal proposed be sweet enough to bring about regime change? We are in a position that we’ve been in multiple times before – letting Trump cook and seeing what comes next.
Featured image: original Victory Girls art by Darleen Click
George V says: Here’s a way out for the Cuban leaders: Offer them high-paying professorships at US universities like Columbia and Harvard. It would be good to have a few professors at these universities who are more conservative than the current bunch. 🙂
Cameron says: Dude, that was exactly the laugh I needed this morning. Thank you.
2 Comments